Collect. Czech. Chem. Commun. 1994, 59, 2282-2292

2α-Alkoxymethyl Cephalosporins: Reactions of exo-2-Methylene Cephalosporin Sulfones with Alcohols

Maxwell D. Cummings, David P. Czajkowski, John Brunstein, Narender A. V. Reddy, Oludotun A. Phillips, Charles Fiakpui, Paul Spevak, Ronald G. Micetich and Samarendra N. Maiti

SynPhar Laboratories Inc., Taiho Alberta Centre, #2, 4290-91A Street, Edmonton, Alberta, Canada T6E 5V2


A series of 2α-alkoxymethyl cephem sulfones were prepared by nucleophilic addition of a variety of alcohols to exo-2-methylene cephem sulfones. The 2α-alkoxymethyl group was introduced with the aim of improving the inhibitory activity against human leukocyte elastase (HLE) over the unsubstituted compounds. However, against HLE the in vitro activity was still inferior to that shown by the C-2 unsubstituted cephem sulfones.